5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione

In the title compound, C10H9FN2O2, the dihedral angle between the hydantoin unit and the benzene ring is 65.55 (5)°. The atoms in the hydantoin ring are coplanar, with a mean deviation of 0.015 Å and a maximum deviation of 0.075 (2) Å for one carbonyl O atom. N—H⋯O hydrogen bonds link the molecules into one-dimensional chains, with one carbonyl group acting as a bifurcated acceptor and the other accepting no hydrogen bonds.

In the title compound, C 10 H 9 FN 2 O 2 , the dihedral angle between the hydantoin unit and the benzene ring is 65.55 (5) . The atoms in the hydantoin ring are coplanar, with a mean deviation of 0.015 Å and a maximum deviation of 0.075 (2) Å for one carbonyl O atom. N-HÁ Á ÁO hydrogen bonds link the molecules into one-dimensional chains, with one carbonyl group acting as a bifurcated acceptor and the other accepting no hydrogen bonds.
MKR is grateful to the Higher Education Commission of Pakistan for financial support under the International Support Initiative Program for a Doctoral Fellowship at Gifu University, Japan.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2269).

Comment
Active research is being carried out in this laboratory on the synthesis of sulfonyl cyclic ureas and their evaluation as hypoglycemic agents (Ahmad et al., 2002;Ahmad et al., 2000). Imidazolidine-2,4-diones, a class of cyclic urea molecules, exhibit diverse biological activities like anti-cancer (Sheppeck et al., 2007), anti-viral (Rajic et al., 2006), COX-2 inhibitors (Park et al., 2007) and hormone receptor antagonists (Balavoine et al., 2007). The title compound ( Fig. 1) was synthesized as an intermediate for onward conversion to sulfonyl derivatives for hypoglycemic assay. It contains a hydantoin ring attached to a methyl and p-flourophenyl group at the chiral centre C1. All bond distances are in agreement with experimental values found in similar compounds. The atoms in the hydantoin ring are planar as expected (Mullica et al., 1998)

Refinement
H atoms bound to N atoms were located in difference Fourier maps and refined freely with isotropic displacement parameters.
Other H atoms were placed in idealized positions and treated as riding, with C-H = 0.95-0.98 Å and with U iso (H) = 1.2 or 1.5U eq (C). Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.